Triethoxysilane
Recent Literature
A family of chiral iminophenyl oxazolinylphenylamines (IPOPA) ligands enables an
efficient cobalt-catalyzed asymmetric hydrosilylation of simple ketones with a
low catalyst loading of CoCl2 to afford chiral alcohols in good
yields with high enantioselectivities.
X. Chen, Z. Lu, Org. Lett.,
2016, 18, 4658-4661.
A zinc-catalyzed reduction of tertiary amides shows remarkable chemoselectivity
and substrate scope tolerating ester, ether, nitro, cyano, azo, and keto
substituents.
S. Das, D. Addis, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc., 2010,
132, 1770-1771.
Transition-metal-free catalytic protocols for controlled reduction of amide
functions using cheap and bench-stable hydrosilanes as reducing agents enable
the selective reduction of unactivated C-O bonds in amides. By altering the
hydrosilane and solvent, the C-N bonds selectively breaks via a
deacylative cleavage.
W. Yao, L. He, D. Han, A. Zhong, J. Org. Chem., 2019, 84,
14627-14635.
A simple, mild, catalyst-free, and efficacious KOtBu-mediated
reductive cyanation reaction of tertiary amides provides a series of
α-aminonitriles in good yields under hydrosilylation conditions with good
functional group tolerance. The reaction works well with readily available amide
substrates, cheap KOtBu, and a commercially available hydrosilane (EtO)3SiH
and the workup is convenient.
L . Liu, Y. Liu, X. Shen, X. Zhang, S. Deng, Y. Chen, J. Org. Chem., 2022, 87,
6321-6329.
A highly regio- and enantioselective copper-catalyzed reductive
hydroxymethylation of styrenes and 1,3-dienes with 1 atm of CO2
readily provides important chiral homobenzylic alcohols. Moreover, various
1,3-dienes were converted to chiral homoallylic alcohols with high yields and
excellent regio-, enantio-, and Z/E-selectivities.
Y.-Y. Gui, N. Hu, X.-W. Chen, L-L. Liao, J.-H. Ye, Z. Zhang, J. Li, D.-G. Yu, J. Am. Chem. Soc., 2017,
139, 17011-17014.
A nickel hydride-catalyzed hydroacylation of aryl alkenes using aroyl
fluorides proceeds without recourse to an exogenous ligand under mild conditions.
The synthetic utility of the present method is demonstrated by a glovebox-free,
gram-scale reaction and late-stage derivatizations of complex molecules.
J. Kim, J. Jang, Y. Lee, K. Shin, Org. Lett.,
2022, 24, 5412-5416.
An enantioselective Ni-catalyzed reaction of an alkyl halide (derived from an
aldehyde and an acyl bromide), an olefin, and a hydrosilane provides esters of
chiral dialkyl carbinols. The method is versatile and tolerates substituents
that vary in size and that bear a range of functional groups. A four-component
variant of this process, wherein the alkyl halide is generated in situ, is also
reported.
Z.-P. Yang, G. C. Fu, J. Am. Chem. Soc.,
2020, 142, 5870-5875.
An efficient rhodium-catalyzed method allows the preparation of
aryltriethoxysilanes from arenediazonium tosylate salts. A new method for
hydrodediazoniation has also been explored.
Z. Y. Tang, Y. Zhang, T. Wang, W. Wang, Synlett, 2010,
804-808.
A bimetallic
catalyst system composed of a group 4 metallocene difluoride and palladium dichloride
enables a reductive cross-coupling of alkynes and aryl halides to provide (E)-alkenes
in the presence of a hydrosilane and NaF. This reaction proceeds via an in situ generated alkenyl
metallocene intermediate derived from the group 4 metallocene difluoride.
K. Takahashi, H. Morishita, Y. Ogiwara, N. Sakai, J. Org. Chem., 2018, 83,
13734-13742.
An inexpensive aminoguanidine efficiently catalyzes a reductive cyclization
of o-phenylenediamines with CO2 in the presence of
triethoxysilane. Various functionalized benzimidazoles, benzoxazole, and
benzothiazole were synthesized in high yields. Mechanistic studies indicate that
formic acid acts as a cocatalyst.
Y. Sun, K. Gao, J. Org. Chem., 2023, 88,
7463-7468.
